IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Developmental and genetic mechanisms underlying seedlessness in grapevine somatic variants

Seedless table grapes are greatly appreciated for fresh and dry consumption. There is also some interest in seedless winegrapes, because the combination of lower fruit set, smaller berries with higher skin/pulp ratio and looser bunches with the absence of seeds in crushed berries, a possible source of astringent tannins, might also have favorable effects on wine quality.
The gene VviAGL11 has been shown to play a central role in stenospermocarpy in Sultanina, but the molecular bases of other sources of stenospermocarpy as well as of parthenocarpy have not been clarified yet.

Interaction Between Armenian Clay-based Ceramic and Model Wine

Clay-based ceramic vessels (jars, pyhtoi, etc.) for wine fermentation and aging processes have been used in several cultures for millennia. This know-how still in practice in several countries of the Armenian highland is gaining worldwide in curiosity, popularity, and interest. Ceramic pots are famous among traditional winemakers for their benefits such as temperature regulation, natural cooling system, favorable oxygen exchange, and impact on pH, which are different from those of stainless steel, wood barrels, or concrete.

Evaluation of the hydroxyethyl radical formation kinetic and Strecker aldehydes distribution for assessing the oxidative susceptibility of Chardonnay wines

Over the last decade, much attention has been paid on the oxidative susceptibility of white wines, given its key role in determining their ageing potential.

Retrospective analysis of our knowledge regarding the genetics of relevant traits for rootstock breeding 

Rootstocks were the first sustainable and environmentally friendly strategy to cope with a major threat for Vitis vinifera cultivation. In addition to providing Phylloxera resistance, they play an important role in protecting against other soil-borne pests, such as nematodes, and in adapting V. vinifera to limiting abiotic conditions. Today viticulture has to adapt to ongoing climate change whilst simultaneously reducing its environmental impact. In this context, rootstocks are a central element in the development of agro-ecological practices that increase adaptive potential with low external inputs. Despite the apparent diversity of the Vitis genus, only few rootstock varieties are used worldwide and most of them have a very narrow genetic background. This means that there is considerable scope to breed new, improved rootstocks to adapt viticulture for the future.

Within-vineyard spatial variation impacts methoxypyrazine accumulation in the rachis of Cabernet-Sauvignon

To investigate the impact of spatial variation in vine vigour on the accumulation of methoxypyrazines in the rachis of Cabernet-Sauvignon. Cabernet-Sauvignon rachis has been shown to contain significantly higher concentrations